A research project into large group decision-making in a New England Town Meeting surprised us with the degree to which sustainability came to be the axis around which political debate revolved. We identified two very different yet overlapping conceptions of sustainability: one emphasized fiscal responsibility; the other asserted the merits of environmental stewardship. Each of the two conceptions had proponents, with strong views about what constituted good versus bad governing practices, each with a strong sense of what was good for the town. In this paper, we sort out those meanings. We seek to understand and expose the contours of sustainability, how the discourses around sustainability enter political processes, and to shed light on ongoing debates about the form of governance best suited for a democratically inclined New England town. Methods involved both quantitative and qualitative approaches, including data collection and analysis activities that comprised four levels: (1) participant observation of the Town Meeting; (2) quantitative analysis of voting behaviors; (3) interviews with 30 of the 240 members of the Town Meeting; and (4) thematic analysis, codebook development, and coding. Finally, in the spirit of contributing to the making of a future possible world, the authors ponder the courses forward for democratic processes and the future of a town caught in a ‘pitched battle’ over the terms and stakes of sustainability.